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Stef and the City

Chicago Matchmaking Services

  • Dating these days is HARD. It’s hard to know where the BEST places are to meet someone.
  • Has it been months since you’ve last had a GOOD date?
  • Are you spending too much time and not enough results?
  • Do you find that it’s hard to find attractive, quality singles?
  • Are you tired of meeting people that don’t look like their pictures?
  • Do you need a new selection of people to meet?
  • Are you finding that you don’t know the “new” dating rules?
  • Has it gotten a lot harder to meet people since you graduated college and since your friends have
    gotten married?
  • Did you recently get divorced and need to get help to get back into dating?
  • Do you feel like you are spending time seeking out dates and not getting anywhere?
  • Do the people you meet are not the quality professional people you are looking for?
  • Are you looking for people that are serious about finding a relationship?
  • Do you find that your social life needs a boost? 

Chicago matchmaker Stef, at Stef and the City is an alternative to costly introduction services that might not have
the types of people you are looking for. We have the BEST prices among Chicago dating services, and offer the BEST options for singles. It’s personalized matchmaking! Not only do we have a great base of clients, but we also continually search for new clients that fit what our clients are looking for.

We continue to bring new people into our service on a daily basis! Whether it’s having our staff go out and about, our constant publicity, or world of mouth- we get NEW people coming in daily to make our service successful! We believe in honesty about what we can provide for you and the timeline that it takes to do so. We would rather wait or search for you than to give you the wrong matches.

Gentleman, we know you are looking for a two-way street in dating. Meet local single women who are also invested emotionally and financially. Let us do the work! Meeting attractive, quality, single women has never been so easy!

Our introduction service stays true to what people need- your own personal recruiter!

  • We vet, screen, and interview each and every person you meet!
  • We invest the time and energy and get you the results you are looking for!
  • We give you the feedback that can make you even more successful in your relationships!
  • Let us find you the next love of your life!
  • What do you have to lose? Fill out our questionnaire today!

It’s no obligation if you fill out a questionnaire, and remember you only have things to gain by contacting us. If we don’t have a match for you today, you never know who we might meet for you tomorrow! You can find an initial questionnaire on our CONTACT US page.

Keep in mind we are MORE than just an introduction service. Be sure to check out all we have to offer under the Services tab at the top of this page. Not only do we handle making introductions, but we have:

  • Matchmaking: We do our specialized, screened matchmaking for both men and women!
  • Dating coaching: New into dating after a long time? Gone through a recent divorce? Unsure why you are not getting the results you want? Get your own dating advisor.
  • Personalized social calendars: Maximize your time by getting assistance with personal life planning. Be where you need to be to meet the people that fit YOUR needs for relationships and friendships.
  • Events: We know where to go! As seen on ABC7, CBS2, NBC5, WCIU’s “You and Me This Morning”, Fox32, WGNWindy City Live and more we tell about the places to be at along with special Stef and the City discounts!
  • Singles travel: Do you need to find places to travel that you are not the only single person? Do you want to travel internationally or abroad? We have the BEST prices and know the 411 on what you need to know!

We cater to MANY ages groups: whether you are single and never married, divorced or widowed in your 20’s, 30’s, 40’s or 50’s, 60’s- we have the people you want to meet! Check out our Casting Call  page- we have new singles listed monthly. We may already have your match!





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